Water → (NZ)-N-[(4S)-4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-ylidene]hydroxylamine

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Reaction Steps

To a solution of (4S)-4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydronaphthalen-1(2H)-one (55) (1.2 g, 3.92 mmol) in CH2Cl2 (30 mL) and MeOH (20 mL) was added NH2OH.HCl (0.41 g, 5.92 mmol) and Et3N (1.19 g, 11.84 mmol). The reaction mixture was heated at reflux. After 1 h, H2O (10 mL0 was added and the resultant mixture was heated at reflux for 5 h before being concentrated. The residue was purified by silica gel column chromatography (ethyl acetatelhexane=1:7 to 1:5). Oxime 57, eluted from the column first (0.51 g, 41%) followed by the oxime 58 (0.49, 39%).

Provenance & Evidence